p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 131721904, compound

HRID 2289042Notes

Reaction equation

HRID 2289042 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:8](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[OH:41][C@H:42]([C@@H:65]1[CH2:69][C@H:68]([SH:70])[CH2:67][N:66]1[C:71]([O:73][CH2:74][C:75]1[CH:80]=[CH:79][C:78]([N+:81]([O-:83])=[O:82])=[CH:77][CH:76]=1)=[O:72])[CH2:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:52]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][CH:57]=2)=[O:53])[CH2:48][CH2:47]1)=[O:45]>>[OH:1][C@@H:2]([C@H:4]1[C:39](=[O:40])[N:6]2[C:7]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:27])=[C:8]([S:70][C@@H:68]3[CH2:67][N:66]([C:71]([O:73][CH2:74][C:75]4[CH:80]=[CH:79][C:78]([N+:81]([O-:83])=[O:82])=[CH:77][CH:76]=4)=[O:72])[C@H:65]([C@@H:42]([OH:41])[CH2:43][C:44]([N:46]4[CH2:47][CH2:48][N:49]([C:52]([O:54][CH2:55][C:56]5[CH:57]=[CH:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=5)=[O:53])[CH2:50][CH2:51]4)=[O:45])[CH2:69]3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

3

Reactant 2

HCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 57180962HCID 57180962, compound

Product 1

HCID 131721904HCID 131721904, compoundYield 75.5%

Procedure

By using 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-(diphenylphosphoryloxy)-1-carbapen-2-em-3-carboxylate (461.1 mg) and (2S,4S)-2-[(1S)-1-hydroxy-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-ylcarbonyl]ethyl]-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (456.2 mg), reaction and purification were carried out in a similar manner to that described in Example 40-(1), whereby 4-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-2-[(2S,4S)-2-[(1S)-1-hydroxy-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-ylcarbonyl]ethyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-methyl-1-carbapen-2-em-3-carboxylate (536.7 mg) was obtained.

Sources & evidence

ORD record
ord-a5e2a2bfaacb44ff824d03efe7e92eb7
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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